1,4-Dihydroxy-2,3-dinitro-9,10-anthraquinone

Abstract

In the title compound, C14H6N2O8, the anthraquinone unit is essentially planar [maximum deviation = 0.0645 (10) Å], and there are two intramolecular O–H...O hydrogen bonds formingS(6) motifs. The planes of the two nitro substituents make dihedral angles of 54.77 (8) and 55.60 (3)° with the anthraquinone ring system. In the crystal, molecules are linked by short intermolecular O...O contacts, leading to a three-dimensional network structure.

Charge-Transfer Complexes of Linear Acenes with a New Acceptor Perfluoroanthraquinone. The Interplay of Charge-Transfer and F···F Interactions

“…Perfluoroanthraquinone was first studied in 1973 with visual registration of the reflections’ intensity; thus, we decided to redetermine its crystalline structure using modern facilities and low temperature. The notable feature of the PFAQ molecule is the folded structure of its carbon skeleton (Figure ); two planes involving terminal aromatic rings intersect along the central C–C direction with the torsion angle 19.7°, in contrast to planar anthraquinone − or some of its derivatives with hydroxyl groups attached to carbons at 1 or 8 positions. − This distortion of planarity is caused by the repulsion between the oxygen atoms and the neighboring fluorine atoms, which results in unusual conformation of the quinone ring. The central six-membered quinone ring adopts the boat conformation with carbon atoms bearing oxygens deviating from the plane of the other four carbons.…”

Crystal structures of 1-hydroxy-4-propyloxy-9,10-anthraquinone and its acetyl derivative

“…Side view of two neighboring molecules of compound (I). (Kitamura et al, 2015b), 1,4-dihydroxy-2,3-dinitro-9,10anthraquinone (Furukawa et al, 2016), 1,4-diethoxy-9,10anthraquinone (Kitamura et al, 2015a), 2-bromo-1,4-dihydroxy-9,10-anthraquinone (Furukawa et al, 2014), 2,6dimethoxy-9,10-anthraquinone (Ohta et al, 2012a), 2,6dipropyloxy-9,10-anthraquinone (Ohta et al, 2012b), 2,3,6,7tetrapropyloxy-9,10-anthraquinone (Ohta et al, 2012b).…”